Yes, it's a town road, but its classification provides for zero maintenance from the town. I own the land, but it's a public right of way. It creates an interesting problem because although I'm willing to maintain it for my own use and convenience, I'm not really allowed to since it's a town road. As you can imagine, taking a backhoe to a town road is generally not socially acceptable behavior. But the town doesn't maintain it either so I'm willing to.... you see the problem.
The solution has been to "consult" the town road agent about how to best maintain it, and to consult with the other land owners along the road (fortunately there are only two) before breaking ground. The road agent was extreemly helpful and walked the whole road with me pointing out how to address the various issues, what size pipe to use for the culverts, etc. He even kicked in some culvert pipe and offered to provide some fill and maybe even a pass or two with a road grader. He preached that it's all about drainage, drainage, drainage. We talked about road fabric, which he loves, but he repeated the need to begin with proper drainage. He was a huge help and I learned a lot.
Getting back to your comment, I've put crushed stone down before to get logging trucks in during harvests, and I don't mind adding more, but I don't want it all to sink to the center of the earth. Brings us right back to drainage. My thinking is to get the drainage all worked out first, then do road fabric followed by stone and/or hard pack (pick your local name for the stuff) where the final surface needs improving.
I'm hoping to get more grading done this fall before the surface freezes and hopefully next spring will be a prettier scene.